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The mol­ecular structure of the title compound, C11H12N2O3S, adopts a cistrans configuration with respect to the positions of the propionic acid and benzoyl groups relative to the S atom across the thio­urea C—N bonds. In the crystal structure, mol­ecules are linked by O—H...S and C—H...O inter­actions, forming a one-dimensional chain parallel to the b axis.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805039607/hk6062sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805039607/hk6062Isup2.hkl
Contains datablock I

CCDC reference: 296720

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.037
  • wR factor = 0.104
  • Data-to-parameter ratio = 13.3

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT420_ALERT_2_C D-H Without Acceptor N1 - H1 ... ?
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Comment top

The title compound, (I), is isomorphous to 3-(3-benzoylthioureido)propionic acid (Yusof & Yamin, 2003) except that the 3-benzoylthioureido group is attached to the α-alanine group. The molecular structure adopts a cis--trans configuration with respect to the position of the propionic acid and benzoyl groups relative to the S atom across the C8—N2 and C8—N1 bonds, respectively.

The bond lengths and angles (Table 1) are in normal ranges (Allen et al.,1987) and comparable to its β- alanine derivative. The central carbonyl-thiourea moiety (S1/C8/N1/N2/C7), phenyl (C1–C6) and ethanoic acid [maximum deviation at C7 of 0.037 (2) Å] fragments are planar. The central carbonylthiourea moiety makes dihedral angles with phenyl and ethanoic acid fragments of 27.52 (9) and 24.20 (12)°, respectively. The phenyl ring is inclined to the ethanoic acid fragment by 4.19 (4)°.

There are three intramolecular hydrogen bonds C9—H9···S1, N2—H2A···O1 and N2—H2A···O3 (Table 2) and, as a result, two pseudo-five-membered rings (C9—H9—S1—C8—N2), (N2—H2A—O3—C11—C9) and a pseudo-six-membered ring (N2—H2A—O1—C7—N1—C8) are formed (Fig. 1). In the crystal structure, the molecules are linked by intermolecular contacts, O2—H2···S1i and C5—H5···O3ii (see Table 2 for symmetry codes), forming a one-dimensional network parallel to the b axis (Fig. 2).

Experimental top

A solution of 2-aminopropionic acid (4.45 g, 0.05 mol) in acetone (20 ml) was added dropwise to 20 ml of acetone solution containing an equimolar amount of benzoyl isothiocyanate in a two-necked round-bottomed flask. The solution was refluxed for about 5 h and then filtered off into a beaker containing ice. The yellow precipitate was washed with cold acetone–distilled water, before drying and kept in a desiccator (yield 10.72 g, 85%, m.p. 430–431 K). Recrystallization from acetonitrile yielded single crystals suitable for X-ray analysis.

Refinement top

H atoms were positioned geometrically [O—H = 0.82, N—H = 0.86 and C—H = 0.93 or 0.96 Å (methyl)] and constrained to ride on their parent atoms with Uiso(H) = 1.2 (1.5 methyl and hydroxyl) Ueq(C/N/O).

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON ( Spek, 2003).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, (I), with displacement ellipsoids drawn at the 50% probability level.
[Figure 2] Fig. 2. Packing diagram of compound (I), viewed down the c axis. The dashed lines denote O—H···S and C—H···O hydrogen bonds.
2-(3-Benzoylthioureido)propionic acid top
Crystal data top
C11H12N2O3SZ = 2
Mr = 252.29F(000) = 264
Triclinic, P1Dx = 1.419 Mg m3
Hall symbol: -P 1Melting point = 430–431 K
a = 7.3570 (18) ÅMo Kα radiation, λ = 0.71073 Å
b = 8.083 (2) ÅCell parameters from 835 reflections
c = 10.706 (3) Åθ = 1.9–25.0°
α = 87.395 (4)°µ = 0.27 mm1
β = 77.128 (4)°T = 298 K
γ = 72.065 (5)°Block, yellow
V = 590.3 (3) Å30.49 × 0.33 × 0.31 mm
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
2076 independent reflections
Radiation source: fine-focus sealed tube1858 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.020
Detector resolution: 83.66 pixels mm-1θmax = 25.0°, θmin = 1.9°
ω scansh = 88
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
k = 99
Tmin = 0.878, Tmax = 0.920l = 1212
5591 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.037Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.104H-atom parameters constrained
S = 1.11 w = 1/[σ2(Fo2) + (0.0479P)2 + 0.2021P]
where P = (Fo2 + 2Fc2)/3
2076 reflections(Δ/σ)max < 0.001
156 parametersΔρmax = 0.21 e Å3
0 restraintsΔρmin = 0.18 e Å3
Crystal data top
C11H12N2O3Sγ = 72.065 (5)°
Mr = 252.29V = 590.3 (3) Å3
Triclinic, P1Z = 2
a = 7.3570 (18) ÅMo Kα radiation
b = 8.083 (2) ŵ = 0.27 mm1
c = 10.706 (3) ÅT = 298 K
α = 87.395 (4)°0.49 × 0.33 × 0.31 mm
β = 77.128 (4)°
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
2076 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
1858 reflections with I > 2σ(I)
Tmin = 0.878, Tmax = 0.920Rint = 0.020
5591 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0370 restraints
wR(F2) = 0.104H-atom parameters constrained
S = 1.11Δρmax = 0.21 e Å3
2076 reflectionsΔρmin = 0.18 e Å3
156 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.05389 (9)0.28808 (6)0.84620 (5)0.0557 (2)
O10.2919 (3)0.4469 (2)0.44662 (14)0.0715 (5)
O20.1648 (3)0.88547 (17)0.87377 (14)0.0632 (4)
H20.14090.98750.85300.095*
O30.2032 (3)0.83654 (19)0.66515 (14)0.0627 (4)
N10.1877 (3)0.2679 (2)0.59569 (15)0.0493 (4)
H10.16030.17140.60450.059*
N20.2135 (2)0.50137 (19)0.69966 (14)0.0445 (4)
H2A0.25830.53510.62500.053*
C10.2774 (3)0.2387 (3)0.24629 (18)0.0486 (5)
H1A0.26480.35490.22850.058*
C20.2974 (3)0.1236 (3)0.14897 (19)0.0558 (5)
H2B0.29870.16250.06580.067*
C30.3153 (3)0.0476 (3)0.1745 (2)0.0596 (6)
H30.32750.12440.10880.071*
C40.3152 (4)0.1057 (3)0.2968 (2)0.0631 (6)
H40.32800.22210.31390.076*
C50.2962 (3)0.0080 (3)0.3946 (2)0.0572 (5)
H50.29680.03220.47740.069*
C60.2762 (3)0.1812 (2)0.37046 (17)0.0443 (4)
C70.2548 (3)0.3113 (3)0.47101 (18)0.0493 (5)
C80.1591 (3)0.3601 (2)0.70800 (18)0.0430 (4)
C90.2007 (3)0.6027 (2)0.81187 (17)0.0408 (4)
H90.07890.60630.87330.049*
C100.3702 (3)0.5220 (3)0.8767 (2)0.0546 (5)
H10A0.36830.40800.90490.082*
H10B0.35790.59350.94920.082*
H10C0.49150.51360.81700.082*
C110.1908 (3)0.7864 (2)0.77254 (18)0.0453 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0881 (4)0.0384 (3)0.0404 (3)0.0303 (3)0.0025 (3)0.0038 (2)
O10.1252 (15)0.0572 (9)0.0426 (8)0.0490 (10)0.0100 (8)0.0020 (7)
O20.1079 (13)0.0339 (7)0.0526 (9)0.0256 (8)0.0215 (8)0.0007 (6)
O30.0986 (12)0.0482 (8)0.0453 (8)0.0320 (8)0.0121 (8)0.0104 (6)
N10.0724 (11)0.0428 (9)0.0366 (8)0.0273 (8)0.0051 (8)0.0043 (7)
N20.0654 (10)0.0378 (8)0.0327 (8)0.0229 (7)0.0057 (7)0.0004 (6)
C10.0562 (12)0.0508 (11)0.0408 (10)0.0211 (9)0.0088 (9)0.0031 (8)
C20.0613 (13)0.0722 (15)0.0347 (10)0.0213 (11)0.0106 (9)0.0001 (9)
C30.0703 (14)0.0617 (14)0.0445 (12)0.0176 (11)0.0082 (10)0.0175 (10)
C40.0882 (17)0.0453 (12)0.0513 (12)0.0157 (11)0.0108 (11)0.0063 (9)
C50.0806 (15)0.0494 (12)0.0370 (10)0.0144 (10)0.0111 (10)0.0001 (8)
C60.0504 (11)0.0460 (11)0.0367 (10)0.0152 (8)0.0084 (8)0.0029 (8)
C70.0633 (12)0.0478 (11)0.0386 (10)0.0198 (9)0.0106 (9)0.0003 (8)
C80.0555 (11)0.0347 (9)0.0383 (10)0.0145 (8)0.0079 (8)0.0018 (7)
C90.0555 (11)0.0329 (9)0.0353 (9)0.0166 (8)0.0081 (8)0.0008 (7)
C100.0668 (13)0.0430 (11)0.0588 (13)0.0165 (10)0.0236 (11)0.0019 (9)
C110.0572 (12)0.0371 (10)0.0441 (11)0.0181 (8)0.0112 (8)0.0013 (8)
Geometric parameters (Å, º) top
S1—C81.6778 (19)C2—H2B0.9300
O1—C71.212 (2)C3—C41.371 (3)
O2—C111.321 (2)C3—H30.9300
O2—H20.8200C4—C51.380 (3)
O3—C111.195 (2)C4—H40.9300
N1—C81.385 (2)C5—C61.380 (3)
N1—C71.385 (2)C5—H50.9300
N1—H10.8600C6—C71.488 (3)
N2—C81.315 (2)C9—C111.509 (2)
N2—C91.454 (2)C9—C101.518 (3)
N2—H2A0.8600C9—H90.9800
C1—C21.381 (3)C10—H10A0.9600
C1—C61.387 (3)C10—H10B0.9600
C1—H1A0.9300C10—H10C0.9600
C2—C31.369 (3)
C11—O2—H2109.5C5—C6—C7123.39 (17)
C8—N1—C7128.30 (16)C1—C6—C7117.59 (18)
C8—N1—H1115.8O1—C7—N1121.72 (18)
C7—N1—H1115.8O1—C7—C6122.86 (18)
C8—N2—C9122.46 (15)N1—C7—C6115.43 (17)
C8—N2—H2A118.8N2—C8—N1117.74 (16)
C9—N2—H2A118.8N2—C8—S1123.69 (14)
C2—C1—C6120.12 (19)N1—C8—S1118.56 (14)
C2—C1—H1A119.9N2—C9—C11108.88 (15)
C6—C1—H1A119.9N2—C9—C10111.97 (15)
C3—C2—C1120.27 (19)C11—C9—C10111.40 (16)
C3—C2—H2B119.9N2—C9—H9108.2
C1—C2—H2B119.9C11—C9—H9108.2
C2—C3—C4120.02 (19)C10—C9—H9108.2
C2—C3—H3120.0C9—C10—H10A109.5
C4—C3—H3120.0C9—C10—H10B109.5
C3—C4—C5120.2 (2)H10A—C10—H10B109.5
C3—C4—H4119.9C9—C10—H10C109.5
C5—C4—H4119.9H10A—C10—H10C109.5
C4—C5—C6120.40 (19)H10B—C10—H10C109.5
C4—C5—H5119.8O3—C11—O2124.35 (18)
C6—C5—H5119.8O3—C11—C9125.10 (17)
C5—C6—C1119.01 (18)O2—C11—C9110.54 (16)
C6—C1—C2—C30.3 (3)C5—C6—C7—N121.8 (3)
C1—C2—C3—C40.6 (3)C1—C6—C7—N1158.69 (18)
C2—C3—C4—C50.3 (4)C9—N2—C8—N1176.40 (17)
C3—C4—C5—C60.3 (4)C9—N2—C8—S14.7 (3)
C4—C5—C6—C10.6 (3)C7—N1—C8—N25.2 (3)
C4—C5—C6—C7179.9 (2)C7—N1—C8—S1173.76 (17)
C2—C1—C6—C50.3 (3)C8—N2—C9—C11156.49 (18)
C2—C1—C6—C7179.83 (19)C8—N2—C9—C1079.9 (2)
C8—N1—C7—O12.5 (4)N2—C9—C11—O34.1 (3)
C8—N1—C7—C6178.01 (19)C10—C9—C11—O3119.9 (2)
C5—C6—C7—O1158.7 (2)N2—C9—C11—O2175.48 (16)
C1—C6—C7—O120.8 (3)C10—C9—C11—O260.6 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C9—H9···S10.982.673.033 (2)102
N2—H2A···O10.862.012.669 (2)133
N2—H2A···O30.862.392.698 (2)102
O2—H2···S1i0.822.323.1190 (16)166
C5—H5···O3ii0.932.303.180 (3)158
Symmetry codes: (i) x, y+1, z; (ii) x, y1, z.

Experimental details

Crystal data
Chemical formulaC11H12N2O3S
Mr252.29
Crystal system, space groupTriclinic, P1
Temperature (K)298
a, b, c (Å)7.3570 (18), 8.083 (2), 10.706 (3)
α, β, γ (°)87.395 (4), 77.128 (4), 72.065 (5)
V3)590.3 (3)
Z2
Radiation typeMo Kα
µ (mm1)0.27
Crystal size (mm)0.49 × 0.33 × 0.31
Data collection
DiffractometerBruker SMART APEX CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2000)
Tmin, Tmax0.878, 0.920
No. of measured, independent and
observed [I > 2σ(I)] reflections
5591, 2076, 1858
Rint0.020
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.037, 0.104, 1.11
No. of reflections2076
No. of parameters156
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.21, 0.18

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SAINT, SHELXTL (Sheldrick, 1997), SHELXTL, PARST (Nardelli, 1995) and PLATON ( Spek, 2003).

Selected geometric parameters (Å, º) top
S1—C81.6778 (19)N1—C81.385 (2)
O1—C71.212 (2)N1—C71.385 (2)
O2—C111.321 (2)N2—C81.315 (2)
O3—C111.195 (2)N2—C91.454 (2)
C8—N1—C7128.30 (16)N2—C8—S1123.69 (14)
C8—N2—C9122.46 (15)N1—C8—S1118.56 (14)
N2—C8—N1117.74 (16)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C9—H9···S10.982.673.033 (2)102
N2—H2A···O10.862.012.669 (2)133
N2—H2A···O30.862.392.698 (2)102
O2—H2···S1i0.822.323.1190 (16)166
C5—H5···O3ii0.932.303.180 (3)158
Symmetry codes: (i) x, y+1, z; (ii) x, y1, z.
 

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